Bob Dylan and Digital Transformation

By 1965, Bob Dylan had positioned himself as a leader in the folk music revival movement. With accolades like “spokesman of a generation” dotting the newspapers, Dylan was at what many considered to be the height of his early career. Dylan became a figurehead for folk enthusiasts who felt there was something unauthentic about electric or rock ‘n’ roll music: it was noisy, gimmicky, lacked substance, as was produced to fuel the establishment. Few of Dylan’s most devoted fans, if any, believed their icon would go anywhere near an electric guitar.

But in March 1965, Dylan released Bringing It All Back Home, which was not only his fifth album but also his first album to feature an electric band accompaniment. And in July of that same year, he performed at the Newport Folk Festival, electric guitar in hand, with a fully amplified band. The three-song set received mixed and even hostile reviews.

On the surface, this historic event is about Dylan’s attempt to implement some new technology into his art, and people hating him for it. But it also highlights a few important lessons about how businesses can better handle and prepare for digital transformation.

The Business of Being Bob Dylan

It’s not a perfect analogy, but the parallels between Bob Dylan’s storied career and running a successful business don’t require a great leap in imagination. Take core values, for instance. Like any successful business, Dylan had a set of core values that he lived by: embrace change, disrupt the status quo, and create art. Dylan also had a target audience and a delivery system (music) through which he reached that audience. From time to time, Dylan needed to pivot and adapt that delivery system. In the end, he created an experience that spoke to people and made them want more, which is something that every business is trying to achieve.

When we talk about digital transformation in business, it’s about more than adopting new software or having different KPIs; it’s about knowing your core values, understanding your audience, and continually improving upon your delivery system to create a better overall user experience. Identifying and sticking to your core values—even when it’s not convenient—will provoke innovation like nothing else can. Although Dylan’s career was defined by evolution—he would later become a born-again Christian, a radio deejay, a Rock ‘n’ Roll Hall of Fame inductee, and a Nobel Prize winner—his core values always stayed the same.

“The Times They Are a-Changin’”

One of Dylan’s defining folk ballads of the 1960s is The Times They Are a-Changin’, wherein he warns people from all walks of life to prepare for and embrace change, or they’ll “sink like a stone.” And while this song carried obvious implications for “writers and critics”, “senators, congressmen”, and “mothers and fathers” to grow with change, few people realized that Dylan actively practiced what he preached. The man was constantly innovating his style and delivery, and the electric guitar was just another manifestation of that.

Businesses, even those with established, well-known brands, likewise need to adapt in order to stay relevant. It could be something as simple as creating a mobile-friendly website or garnering more audience feedback. Adapting your business to changing times doesn’t mean abandoning your core values, but quite the opposite; it’s improving the way you deliver on those values by giving up those processes or assumptions that are no longer relevant, such as, “nobody cares what our website looks like.”

It’s Not about Technology; It’s about Attitude

Despite drawing a hostile response from the folk music establishment (with some disgruntled fans calling him “Judas” in subsequent shows), Dylan would continue to perform electric sets in his shows, often to a mixture of boos and cheers. But for some fans, their criticism wasn’t so much in Dylan’s adoption of the electric guitar (many agreed it sounded fine on the record); they simply felt the amplifiers distorted his message, turning his performance into a “wall of mush.” Others felt the amplifiers made the lyrics difficult to hear.

Let’s be clear: businesses should do all they can to avoid alienating their audience (nobody wants their company Twitter feed getting blown up with tweets using #Judas), and improper user or adoption of technology can lead to that. You don’t want to evolve too fast. When technology interferes with your message, you need to reevaluate how that technology is being used, or if it’s even necessary. True digital transformation is not about the technology at all, but it’s about adapting your attitude and business operations to create better customer engagement.

That being said, successful digital transformation will force you to make hard decisions. You may need to abandon some of your old suppositions, and that can hurt! Dylan was abandoning the notion that folk music needed to remain acoustic.

For better or for worse, Dylan quite literally found a way to amplify audience engagement with the electric guitar. But the controversy was intentional—he wanted to stir the pot! The electric guitar simply became a vessel for that message, but it wasn’t the message itself. And even if people didn’t like him for it, it certainly got them talking.

Breaking Down Silos

Bob Dylan’s first electric performance blurred the lines between folk and rock, and set in motion a long career of diverse collaborations. From collaborations in folk and blues in the early 1960s, Dylan went on to record several tracks with country star Johnny Cash in 1969. Throughout the 1970s, he collaborated with top non-folk musicians, from Eric Clapton to Bette Midler. And in the late 1980s, he co-founded The Travelling Wilburys, a super-group featuring George Harrison, Jeff Lynne, Roy Orbison, and Tom Petty. Sometimes he co-wrote and played guitar, other times he would provide only backup vocals. In any case, he worried less about the barriers of genre, and more about creating art.

We often refer to “breaking down silos” as one of the hallmarks of digital transformation, but what does it really mean for your business? For Dylan, it was about growth through collaboration, and it’s one of the many reasons he remains so relevant. As you approach digital transformation for your business, surround yourself internally with people you can learn from, and externally, look for partners, not vendors. Allow members of different departments to collaborate and innovate.

Digital transformation starts at the top: when employees see that executives are willing to embrace change and try unconventional strategies, innovation will follow.

Digital transformation is a process, and one that will not always go smoothly. Not every innovation will be a hit with your customers, and you may find letting go of old notions surprisingly difficult. But change is inevitable—from the climate, to your customers, to the competition. As you find ways to adapt and innovate, let your core values guide you. Open yourself up to new collaborations and partnerships. Allow technology to carry your message—just don’t let your message be the technology. Like was mentioned at the beginning, successful businesses create an experience that speaks to people and leaves them wanting more. And sometimes that means you have to plug in.